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Co-Crystals of Caffeine and Hydroxy-2-naphthoic Acids: Unusual Formation of the Carboxylic Acid Dimer in the Presence of a Heterosynthon
Journal article   Peer reviewed

Co-Crystals of Caffeine and Hydroxy-2-naphthoic Acids: Unusual Formation of the Carboxylic Acid Dimer in the Presence of a Heterosynthon

Dejan-Krešimir Bučar, Rodger F Henry, Xiaochun Lou, Richard W Duerst, Thomas B Borchardt, Leonard R MacGillivray and Geoff G. Z Zhang
Molecular pharmaceutics, Vol.4(3), pp.339-346
06/01/2007
DOI: 10.1021/mp070004b
PMID: 17489605

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Abstract

A group of caffeine-containing co-crystals of hydroxy-2-naphthoic acids were synthesized and analyzed via single-crystal X-ray diffraction and IR analysis. The imidazole-carboxylic acid synthon was observed in co-crystals involving 1-hydroxy-2-naphthoic and 3-hydroxy-2-naphthoic acid. In the case of 6-hydroxy-2-naphthoic acid, the co-crystal exhibits a hydrogen-bonded carboxylic acid dimer in the presence of a hydroxyl-caffeine heterosynthon. © 2007 American Chemical Society.

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